Hypothetically
by jhoom
Summary: Sam's not sure how to break the news to Dean that he's been dating Eileen for the past few months. Worried about how Dean might react, he comes up with a fool proof plan.


**AN:** First time trying out Writing Prompt Wednesday from unforth-ninawaters - saw one for "But we're already dating" that caught my eye and figured I'd give it a shot :)

Prompt: So, hypothetically, what if I was seeing someone, and hypothetically, we were pretty serious about each other and, hypothetically, I was thinking of revealing that I'd kept it a secret for, like, a long time and WHY ARE YOU LAUGHING SO HARD is it that hard to believe I'd be in a relationship this is exactly why I didn't say anything!

* * *

It takes a lot to make Sam Winchester nervous. Apocalyptic levels of terrible are necessary for him to be remotely phased. There's only so much that can get to you once you've been attached by a demon version of your brother and been possessed by Lucifer.

This, however, is one of the exceptions to that.

He'd walked through his game plan and spent a lot of time getting everything ready. And there was the repeated pep talk going through his head.

 _It's fine Sam. You're over-reacting. There's no reason to be this nervous. Dean is a reasonable human being. Mostly. Usually._

The first step was to make sure they didn't have a case lined up or any other reason to leave. Doing this at home seemed the best way to make Dean comfortable. He even waited until Dean was changing the Impala's oil, going so far as to interrupt the process to make sure there was no escape.

The next step was to get all the supplies. Homemade burgers, lots of beer (no whiskey though, that could make things go south quick), and of course pie. He'd considered making the pie himself, but even the burgers were a little iffy so he decided not to risk it. Instead he went to that little bakery Dean pretended not to know about or like and splurged on a whole pie instead of just a couple slices.

The last, and most daunting, was the actual conversation.

That's where he kinda lost his nerve. Even with the encouraging texts he kept getting. ( _Tell him! You can do this! Just get it over with!_ ) His hands kept sweating and he couldn't stop his right leg from shaking and god these burgers taste terrible don't they-

"So there a reason you went all out for dinner?"

"Huh?" he snaps out of his increasingly panicked thoughts.

"This is like, the first time in months you've made dinner. And the first time in way longer since you actually made something other than your rabbit food. There something going on?"

"No! Of course not!" He flinches at how quickly he answered. With a cough he tries to distract Dean from noticing. "I just wanted to... you know... talk. Catch up."

Dean is looking at him like he's a complete idiot. Moving the food around in his mouth, he gives the most disinterested look possible. "Catch up?" When Sam doesn't respond, he continues. "You know we live together, right? Here, in the bunker? I see you like... every day. What the hell you have to catch up on? How many times a day I take a piss?"

Right, okay, not off to a great start.

"Well, uh..."

 _Think fast, Winchester. What can you ask Dean about that would- Oh, DUH._

"Actually," he says with a pleased little smile, "I was wondering what Cas has been up to lately. I haven't seen him in a bit."

Sam's eyes nearly roll out of his head at the way Dean's whole face lights up at the prospect of talking about the angel.

Maybe it wasn't a great line of questioning, because after five minutes of finding out about Cas' current hunting activities and an update on how things are going with Claire, it becomes a ten minute tangent on appropriate texting etiquette and how, "For the love of god, he needs to let up on all the damn emoticons."

Eventually Sam just gets out the pie to shut him up.

"So, hypothetically..." He knows Dean's giving him about half of his attention, but that's probably for the best anyway. "What if I were dating someone?"

Dean snorts but whatever snarky comment he had is ignored in favor of taking another bite.

"And, hypothetically, let's say me and this person were pretty serious about each other."

His first slice of pie is almost gone and Dean's grabbing a second helping. "Hypothetically? I'm pretty sure you'd actually have to _meet_ chicks before you can start dating them."

" _Dean._ "

With an overly dramatic eye roll, Dean puts down his fork for two seconds to answer, "If you were ever actually dating a real live girl... or guy, whatever... at least let's settle on human, though... If you were ever actually dating a real live human being, I'd be all for it. But realistically, you're not exactly in a line of work that makes that easy."

Sam doesn't answer, just looks quietly at his hands folded in his lap. It takes Dean long enough to get another huge mouthful before he squints and starts eyeing Sam suspiciously.

"Sam..."

A huge sigh he can't quite help.

"Sam... Are you... _dating_ someone?"

It's weird but he feels like _such_ a little brother right now. This is probably what normal brothers do in their normal lives and it's just kind of eerie. He frowns at that, how weird it is to actually have that even if it's just for a moment.

He feels Dean staring at him and realizes he hasn't actually said anything. "Yes," he manages.

Neither of them say anything. Until Dean just starts _laughing_ this full belly laugh. Little pieces of pie flying out of his mouth with how violently he's trying to get in more air. He pushes back his chair from the table to give himself more room to double over and gasp before more laughter just bubbles out.

Sam is stunned for a full minute before he indignantly shouts, "Why are you laughing?!"

But Dean's too far gone and can't stop. Sam grabs the nearest napkin and throws it at his brother. His rude, asshole of an older brother.

"This is why I didn't say anything, you dick!"

Finally, he calms down and settles heavily against the back of his chair. He rubs a tear from the corner of his eye, the occasional giggle still making its way out. "Who the fuck you datin' Sammy? Do you even _know_ any girls?"

"I know plenty of girls!" he snaps. At Dean's expectant look, he huffs a bit before humoring his brother, "Well... there's uh, Jody and the girls. And Donna. And, uh, Eileen..."

Dean looks as though he's about to give him _so much shit_ for the pathetic little list he comes up with until Sam mentions Eileen. He perks up a bit. "Eileen... the deaf chick from the banshee case?"

Oh shit.

Losing the ability to speak, he just nods.

"... So you're dating Eileen?"

Again, he nods.

Sam holds his breath. This is it. Dean knows and now he's going to get so much shit and his brother is going to be mopey for the next week and maybe buying so much beer wasn't a great idea-

"So..." He waits until Sam actually looks at him. Dean's not mad or annoyed or anything else he'd been worried about. If anything, he just looks amused. "When are you bringing her over for dinner?"


End file.
